Salicylaldehyde → 2-[[5-(Acetyloxy)pentyl]oxy]benzaldehyde

HRID 327952

Reaction equation

HRID 327952 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([OH:9])=[C:5]([CH:7]=[O:8])[CH:6]=1.[C:10]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br)(=[O:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:10]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:9][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=1[CH:7]=[O:8])(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 851405-Bromopentyl acetate

Product 1

HCID 199221122-[[5-(Acetyloxy)pentyl]oxy]benzaldehydeYield 43,549.398%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 12.2 g (0.1 mmol) of salicyladehyde, 23 g (0.11 mol) of 5-bromopentyl acetate, 44.2 g (0.3 mol) of anhydrous, granular potassium carbonate, and 700 mL of acetonitrile was stirred and refluxed for 20 hr. After being cooled, the resulting mixture was filtered with suction and the solids were washed well with ether. The filtrate and washes were combined and concentrated in vacuo giving a yellow oil which was purified by flash chromatography on silica gel, eluting with 4:1 hexane-ether. There was obtained 10.9 g (43.6%) of 2-[[5-(acetyloxy)pentyl]oxy]benzaldehyde as an oil.

Workup

  1. temperaturerefluxed for 20 hr
  2. temperatureAfter being cooled
  3. filtrationthe resulting mixture was filtered with suction
  4. washthe solids were washed well with ether
  5. concentrationconcentrated in vacuo
  6. customgiving a yellow oil which
  7. customwas purified by flash chromatography on silica gel
  8. washeluting with 4:1 hexane-ether

Sources & evidence

ORD record
ord-96c76a38e9b4404eaa89b1c139393c2e
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Linked notes

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